Review of Betting on You by Lynn Painter

Check out my Review of Betting on You by Lynn Painter. I am all about the 1990s! I love reading about the 1990s! Well, while this book was 1990s inspired, it was set in the present (which I think was a mistake).
Betting on You by Lynn Painter
Published on November 28, 2023 by Simon & Schuster
Plot Summary of Betting on You by Lynn Painter
Bailey first meets Charlie when she’s a young teenager, headed home to Omaha on a flight from Alaska where she visiting her divorced dad. Charlie is SO annoying, she thinks.
A year later, Bailey starts a new job at a hotel waterpark in her hometown. Who is her new colleague? Of course, it’s annoying Charlie.
Bailey and Charlie see each other a bit differently now. As they spend more time together, they get more friendly, even a bit flirty. But Charlie, citing a very old movie he once saw, insists that members of the opposite sex can’t just be friends. Bailey is determined to prove him wrong.
Bailey and Charlie keep in touch through high school and before long, they are forced into a fauxmance so that a sympathetic Charlie can serve as a buffer for Bailey against her mom’s new boyfriend.
Can Bailey and Charlie actually be a couple? Maybe. But Charlie is also keeping a secret that might destroy everything.
My Review of Betting on You by Lynn Painter
Betting on You feels like a mash-up between The Statistical Probability of Love at First Sight (in which a teen couple meets on a plane during a time when each of them is in the midst of family drama) and When Harry Met Sally, which is referenced by Charlie in the book.
Things I Liked About Betting On You
To me, Bailey’s experience felt like a very accurate and heartfelt portrayal of what it’s like to be a child of divorce.
Bailey’s anguish as her mom moves on with a new guy was really moving. She wants her mom to be happy, but is truly distraught and heartbroken that she has to share her mom with a new stranger and accept even more changes in her life.
Okay, the SECRET THAT MIGHT DESTROY EVERYTHING is the secret in just about every teen movie of the 90s! But I don’t hate it.
Things I Liked Less About Betting On You
Betting on You is a very LONG book for a teen contemporary romance.
It’s over 400 pages. I will give the book a pass on this because it covers YEARS. But I have to confess that it dragged for me at times.
It’s dialogue heavy (or, as Charlie would say, “talkie”). A lot of the book is flirty conversations alternating with angsty internal monologues. If you like a “banter book,” this one will be perfect for you!
The other thing I’d say is that:
Betting on You felt targeted to an older audience than teens in 2023.
The tone was adult-y.
The slang felt dated. I asked the young adults in my life if they knew what “macking on” meant and they were completely mystified.
Charlie’s inner dialogue, to me, was a bit cringy. Yes, he swears a lot but I feel the Gen Z’s in my life do NOT swear much.
Charlie’s nickname for Bailey is “Glasses.” Huh?
That brought me back to my own 80s childhood. The whole glasses thing reminded me of Jan in the Brady Bunch crying because Bobby told her glasses make her look “goofy.”

Is Bettting On You a Retelling of the 1989 movie When Harry Met Sally?
I haven’t seen the movie in a few years, but there are many parallels.

Harry and Sally meet and then don’t see each other for a while, just like Bailey and Charlie.
Harry tells Sally that men and women can’t be friends, because “the sex part” always gets in the way.
Sally is very picky when ordering her food, and Bailey drinks half Coke half Diet Coke for reasons that escaped me. To balance out the sugar with the chemicals?
I Wish Betting on You Had Been Set in the 1990s
A 90s setting for Betting on You could have also incorporated all the weird throwback aspects of the book like:
–shock over parents getting divorced (in 2023, unconventional families are the new conventional families)
–excessive soda consumption (do teens still drink soda? All the ones I know carry Yetis and Hydroflasks)
– the idea that “men” and “women” can’t be friends (such a weird idea to Gen Zs, who are all about gender fluidity)
–making fun of people’s glasses (Bobby Brady, you should be ashamed of yourself. But I really recommend that Brady Bunch episode)
–that SECRET that has been threatening to destroy everything since the 90s.
Spoiler Below:
A co-worker calls Bailey tightly-wound and bets Charlie $100 that he can’t “get with her.” See Cruel Intentions, She’s All That, Ten Things I Hate About You… etc.
In sum, if you’re an older reader who loves a banter-y book that will “hit you in the feels,” as we used to say in the aughties, grab this one.
If you’re an actual teen, a lot of the book might make you go “huh?” But you’ll understand your parents better.
Did you read this? Will you read it?


